Guns and Briefcases
by stargazer420
Summary: Vanessa is an intelligent and accomplished young woman with her eyes set on becoming the best lawyer in Woodcrest. But, when an unbelievably handsome gangsta barges his way into her life, will she realize that all she's reaching for isn't as picture-perfect as it seems? RileyxOC , with a little CindyxOC. [Rating could change...]
1. Her Name is Vanessa

_Chapter One: Her Name is Vanessa_

"Nigga you cheatin'!"

"Ain't nobody cheatin', nigga! Ya skills is just that weak."

Riley laughed evilly as he and his homeboy, Nico, sat in Nico's living room playing Mortal Kombat. Riley met Nico in high school. Huey had just graduated and was off to college, causing Riley to look for someone new to hassle. Nico was the new kid on the block. He, aside from Cindy McPhearson, was the only real nigga he knew that was his age; once they all started hangin' out, they became untouchable. Nobody could fuck with them; even more so now that they all were in their early twenties.

Plus, with Nico bein' that type of lightskin nigga that all the girls want to get with, he brought plenty of bitches to the table. But, unfortunately for them, he and Cindy had been dating since they formed their trio. It was awkward for Riley to be the third wheel, but he got bitches with no problem regardless.

"No! No!" Nico growled and stood from the couch. Riley had been hitting all the right combos, and Nico was struggling to find a way to come back—like he wasn't already near death. He was losing badly, and he didn't like it, and Riley laughed heartily at his expense.

"Aw yeah, nigga!" Riley stood with him, their fingers smashing the buttons on their controllers in tandem. "Take this ass whoopin'—no homo!"

"…Gay as shit," Nico mumbled. He threw the controller once Riley got him with a fatality, and smacked his hand out of his face as he laughed at him.

"Damn Nico! I knew you wasn't no good, but I ain't know you was this bad!"

"I'm not," Nico said defensively. "I was just using the bad controller…"

Riley continued to laugh and waved his hand at him. "Whatever, nigga. Just give me my money."

Nico grumbled under his breath and stormed out of the living room, probably to go get the twenty dollars they'd bet on the game. Riley sighed and slumped back down on the couch. Cindy was supposed to be there soon—she had some tree that she wanted them to spark up, and he couldn't wait. Then, as if on cue, Nico's doorbell rang.

"Riley get the door! I think it's Cindy." Nico yelled from upstairs.

"Aight," Riley yelled back and walked towards the front of the house.

"Took yo ass long enough," Riley said, loud enough for her to hear behind the door as he undid the locks. He threw the door open, coming face-to-face with a smiling, brown-eyed beauty. She was tall, had smooth-looking caramel skin, and long dark hair tied up in a ponytail. Riley looked her up and down, taking in her sweet curves and innocent face.

She definitely wasn't Cindy.

"Uh…Sorry to bother you." Riley looked up at the woman. Her voice was so light. "Does Nicolas Owens live here?"

 _Nico?_ Riley cleared his throat. "Yeah, he live here."

The woman smiled with relief. "Oh good. Is he home?"

 _The fuck? Nico bringin' side bitches to the crib now?_ Riley smirked at his thoughts and despite himself, he reached for her hand, taking it in his. Her skin was soft. "Can I ask who's askin', beautiful?"

The woman chuckled nervously and slipped her hand away from him. "Vanessa."

Damn, her name was just as sexy as she was. "That's a nice name. It's pretty, like you."

"Thank you, uhm… Who are you?"

"Riley, but everybody 'round here call me Young Reezy."

"Oh." Vanessa tried to bite back the bemused smile on her face. (This guy must be joking). "Well, it was nice meeting you…Riley. I think I'll just come by again tomorrow."

She turned to leave when Riley grabbed her hand again. "My bad, shawty. I ain't scare you or nothin', did I?"

Vanessa shook her head. "Oh, no. I'm just kind of in a hurry right now. Could you tell Nicolas that I stopped by, please?"

"Sho' thing, cutie."

Vanessa took back her hand and Riley watched her walk away from the door. His eyes drifted down to her small waist and round ass and he bit his lip, hoping he would be by here tomorrow to see _that_ again.

"Ayo Riley, is that Cindy or nah?" Nico came downstairs and handed Riley the twenty dollars he owed. Riley snatched it from him and stuffed it in his pocket.

"Nah. It was some pretty little thing. You know Cindy bitch ass always late, we might as well just spark up without her." Riley shrugged and was about to shut the door when—

"What you say, nigga?!"

As he was closing the door, Cindy appeared and pushed it back. Riley jumped in surprise. "Damn nigga, where you come from?!"

"What you mean? I was getting' us some weed!" Cindy shouted, throwing some plastic bags full of green herbs at him. She pushed past Riley and went to Nico, kissing his lips like they used to do in the hallways back in school.

"Ugh, go somewhere else with that shit." Riley growled and walked back to the living room with the weed.

"Don't be mad, Reezy," Nico laughed. "And don't start without us!"

"Shut up!"

* * *

 **A/N: Hello everyone, and thanks for reading this first chapter! I have been wanting to do a Boondocks fanfiction for a while and I think I finally have the plot for one! But I'm not a fan of how short this chapter is (I think it's short). Expect the next chapter to be a bit lengthy (that's when the actual plot kicks off!).**

 **~stargazer420**


	2. New City, New Life

_Chapter Two: New City, New Life_

Vanessa drove through the busy city streets of Woodcrest, the bright buildings and trees passing by her in a colorful blur. The ride over there from Pennsylvania had been fairly short—only a half-hour—but she wanted some time to kill before having to move into her new apartment (and Lord knows how long _that_ could take).

So here she was, on her way to visit her half-brother Nicolas, whom Vanessa hadn't seen since she was little. When their parents split up, he ended up with his father, and she with their mother. Vanessa grew up in the urban streets of Philadelphia, while Nicolas supposedly moved here to Woodcrest.

Now that they both were significantly older and no longer held back by their parents, there was nothing stopping them from seeing each other anymore, like old times.

At a red light, Vanessa took the time to look at the address she'd written down on a piece of paper. He messaged it to her the last time they talked on Facebook. Feeling confident of the reminder, she turned another corner once the light turned green and drove into a small neighborhood.

After skimming past a few houses, Vanessa parked her car outside of the house she assumed was her brother's, got out, and went towards the front door. With a deep breath of encouragement, she rang the doorbell. For a moment there was silence. Then, she heard heavy footsteps.

"Took yo ass long enough."

Vanessa smiled bemusedly. _Did he know I was coming?_

The door flew open, and the person standing there was not her brother. Instead, it was a guy (taller than her) with tan skin, muscular arms, and cornrows. He was good-looking, Vanessa decided, but she hoped that she didn't come to the wrong house—because that would've been embarrassing.

"Uh… Sorry to bother you," Vanessa said to him, as politely as she could. "Does Nicolas Owens live here?"

The man cleared his throat, his Adam's apple bopping up and down. "Yeah, he live here."

Vanessa smiled with relief. Her sense of direction wasn't so bad after all. "Oh good. Is he home?"

The man took her hand in his, catching her by surprise. His thumb was rubbing the backside of her hand, feeling her skin. "Can I ask who's askin', beautiful?"

 _Whoa there…_ Not knowing what else to do, Vanessa chuckled and slipped her hand away from him. "Vanessa."

"That's a nice name," he said. "It's pretty, like you."

"Thank you, uhm… Who are you?"

"Riley, but everybody 'round here call me Young Reezy."

"Oh." Vanessa bit back her bemused smile. Was he serious? _Young Reezy_? At least Nicolas's taste in friends hadn't changed. "Well, it was nice meeting you…Riley. But I think I'll just come by again tomorrow."

Vanessa turned to leave. She was hoping she didn't sound like she was a hurry to get away from him, but then he grabbed her hand again. "My bad, shawty. I ain't scare you or nothin', did I?"

Vanessa shook her head. "Oh, no. I'm just kind of in a hurry right now."

It was true; she almost forgot about her apartment. She had things to unpack, and she still had to meet with her new landlord. "Could you tell Nicolas that I stopped by, please?"

Riley gave her a sweet smile. "Sho' thing, cutie."

Vanessa turned away from him to hide her blush and took back her hand. She felt his eyes on her as she walked back to her car, but was too nervous to turn back. She felt instant relief once she got back in her car and drove off to her next destination.

* * *

Vanessa parked her car in front of an old apartment building. It was only a little bit past the time she was supposed to be there—she hoped that her landlord wasn't too strict on things like that.

She hurriedly left her car and went inside the lobby of the complex. Instantly, she was greeted by a man; he was about her height with dark skin and a lean build.

"Hello," he said. "You must be Vanessa Wellens."

Vanessa smiled and shook his outstretched hand. She recognized his voice from their many phone calls. "Yes, I am. And you must be Donte."

"Yes, it's nice to finally meet you."

Donte gave her a kind smile before ushering her to an elevator. "Your room is on the third floor. I'll gladly show you around."

And so he did. He gave Vanessa a quick walk-through of her apartment. Her living room wasn't too bad and the kitchen wasn't terribly small, and her bedroom was a nice size. All she really thought the apartment needed was a fresh coat of new paint. Maybe she could go get some tomorrow.

"And there you have it. Your rent is due every first of the month." Donte handed Vanessa the key to her new home and proceeded to leave with a farewell smile. "Welcome to the city, Vanessa."

"Thanks, Donte!"

Vanessa shut the door and smiled to herself—her dreams were finally becoming reality! First, she became the first person in her family to graduate college, and now here she is living in her own home!

Well, almost. She still had to unpack her things.

The only thing left on her bucket list was to nail her job interview at Wuncler Law Firm, which was in a week. She'd been hoping for a chance to become a lawyer ever since she was a kid, and after going to the best schools Vanessa's mother and her grades could get her into, she could finally say that her work was about to pay off.

Vanessa sighed with contentment, then she look around at her surroundings. The room was empty - her things were in the trunk of her car.

 _Ugh_ , she groaned. _Better to do it now than later._

* * *

The next morning, Vanessa awoke bright and early on her air mattress. It was a good call bringing it since her new bed wouldn't be here until a few hours later, along with some more furniture she'd ordered online.

Vanessa yawned and left to go shower and wash her face. It was weird starting her day like this—alone and without her mother. Shutting off the faucet, Vanessa went back into her bedroom and searched for her phone. When she found it, she dialed her mother's number.

 _"Oh, praise the Lord!"_ Miss Wellens answered with a cheery tone. _"My baby's okay."_

Vanessa chuckled. "Good morning, mom."

 _"Good morning, sweetie. I thought I told you to call me as soon as you got into town?"_

"I know, I'm sorry. I was just really busy meeting my new landlord and unpacking. I still have plenty more to do."

There was a few seconds of silence over the line, until Miss Wellens finally asked, _"Did you go see Nicolas?"_

Vanessa cleared her throat before answering. "Kind of. I went to his house, but I didn't see _him_."

 _"Hm."_

Nicolas had always been a touchy subject to talk about with Vanessa's mother. He was her firstborn child, and when he and Vanessa's parents split, it was like half of her world had been taken from her. She had always been a great mother to Vanessa regardless, but there was no denying that noticeable emptiness everyone saw in her.

" _Well, maybe you could stop by there again and ask him to help you get settled. Lord knows how much stuff you like to hoard,"_ Miss Wellens continued.

Vanessa flashed a relieving smile at her mother's change of attitude. "Maybe you're right."

 _"Of course I am. I'm your mother."_

The two shared a laugh. It was nice to hear it, especially now that the two were apart. _"Well, I won't keep you on the phone much longer. I know how busy you are."_

"Okay, mom. Love you."

 _"Love you too. And don't forget to go grocery shopping!"_

Vanessa hung up after she said that and rolled her eyes playfully. Of course, even though she was miles away, her mother would still find a way to baby her. But…she was right. Vanessa had no food, no breakfast to start her day.

She would go shopping later, but for now, there had to be someplace nearby for her to eat at. After throwing on some clothes, Vanessa then took it upon herself to explore the streets of Woodcrest.


	3. The Cross-Walk

**Guns and Briefcases  
** _Chapter Three_

Riley awoke that morning at his grandfather's house. He was in his old bedroom, sprawled out over his bed and still wearing yesterday's clothes. He had been out all night with Nico and Cindy—whatever they smoked really fucked him up—and he vaguely remembered anything else. Not that he really cared.

Sitting up slowly, Riley clutched his growling stomach; there was a heavenly smell coming from the kitchen, luring him out of bed to see what whoever was cooking. He lazily followed the scent, his nostrils flaring as he left the room and went downstairs.

He walked into the kitchen and sat down at the table, nodding his head towards his grandfather standing by the fridge. "Waddup, Granddad. What's for breakfast?"

Granddad glared down his grandson and flung an empty Tropicana jug at him, smacking him right in the face. "What the—! Granddad!" Riley yelled, eyes widening in confusion at the man standing in front of the open refrigerator.

"Don't 'Granddad' me. You drank all my orange juice again, boy!" Granddad slammed the refrigerator door shut. Riley stared at his grandfather, still not over the fact that he just threw a jug at him. "Damn, did you have to throw that at me though?"

"Yes, because you don't listen. You just so damn hardheaded." Granddad reached in his pockets and pulled out his car keys, throwing them in Riley's direction. He caught it was ease this time. "Go to the store and get me two more jugs. You can have yo breakfast when you come back."

Riley sucked his teeth and stood. "You could've just said that without bein' all extra, Granddad." He was storming his way out of the kitchen, then stopped suddenly at the threshold. "What, you not goin' give me no money?"

"Your fault, your money." Granddad said before shooing him off. "And take a shower before you go, boy. I can smell you from here."

Riley scrunched up his face in annoyance before finally leaving the kitchen. Robert Freeman was still as stubborn as always, despite his age. He irked Riley to no end, but with Huey gone, there was no one else around to take care of him. _Fuck_ , was all he could think.

* * *

Riley drove out of the neighborhood and into the already bustling city of Woodcrest in his grandfather's car, Dorothy. He remembered the day she got fixed on Pimp My Ride; he and Granddad were so hype. It's not surprising how they were both still able to maintain her fresh look, even after all these years.

He came to a red light and slumped back in the driver's seat, watching as people strode by on the cross walk in front of him. As they walked, he noticed a woman wearing jeans and a t-shirt strut by the car. She seemed familiar, but looked like she was lost. His eyes trailed her body down to her swaying hips, and he smirked in remembrance—he could never forget a nice ass like that.

The light turned green and Riley turned Dorothy down the road she was walking. He hadn't used a turn signal, causing the cars behind him to honk angrily, but he just gave them all the finger and kept moving.

"Vanessa!" Riley shouted out the window. He slowed Dorothy down to a crawl so he could keep up with her pace. The woman turned to him with wide eyes, surprised to see a man she barely knew shouting her name. "Remember me?"

Vanessa stopped walking and squinted her eyes at him, taking a good look at his face. "Riley, right?"

Riley smiled, glad that she could recall his name. "Yeah, that's me. What you doin' out here by yo-self?"

"I was just…on my way to get something to eat." She pulled her hair behind her ear shyly, feeling Riley's stare on her. "Do you know any place nearby I can get to?"

Riley smirked again. He knew she was lost—he could see it all in her cute ass face. "Yeah. There's a small fast food joint 'round the way. Get in the car, I'll take you."

Vanessa's eyes widened and she shook her head. "Oh, no thank you. I'm sure you have plenty of other things to be doing right now. I can just walk there."

She spoke so properly to him, and it couldn't have been more adorable. He had to know where she came from, 'cause it damn sure wasn't here. "Naw, come on, it's real close by. I don't bite."

Vanessa nibbled on her bottom lip as she contemplated taking his offer. Then, much to Riley's surprise, she walked to the passenger side of the car. He unlocked the door for her and she got in, her eyes locking with his.

"Thank you," she told him, her cheeks burning when he smiled back.

"I told you, I don't bite." Riley replied, moving Dorothy down the road and towards the nearest Wuncler-affiliated restaurant.


End file.
